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Chicago Holidays 2025 & 2026

Let’s get your Chicago holiday in the diary. Our friendly Travel Specialists can put together the perfect trip, with Chicago packages from just £675pp.
Let’s get your Chicago holiday in the diary. Our friendly Travel Specialists can put together the perfect trip, with Chicago packages from just £675pp.
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Let’s get your Chicago holiday in the diary. Our friendly Travel Specialists can put together the perfect trip, with Chicago packages from just £675pp.
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Relaxing on the border of Lake Michigan, Chicago, known as “The Windy City” offers a rich music history and an attractive skyline to boot. 
Chicago’s strong musical history is epitomised by its impressive blues and jazz roots along with its world renowned theatre productions. Year after year, Chicago’s calendar is filled to the brim with exciting events and must see attractions everyone can get involved in. 
Welcoming families, couples and groups of all sizes, Chicago opens its cosmopolitan city arms to anyone from all walks of life wanting to explore its beautiful streets, awe-inspiring skyline and cultural treats. Best not forget some of America’s most famous landmarks as well, including the Willis Tower and the quirky Cloud Gate.
  • Winner of British Travel Award 2020

    Winner of British Travel
    Awards 2020

  • 24/7 Florida Help Centre

    24/7 Florida Help
    Centre

  • UK’s No.1 Independent Florida Specialist

    UK’s No.1 Independent
    Florida Specialist

  • Customer Reviews

    98% Customer Reviews

  • Established In 2004

    Established
    In 2004


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Call our Travel Specialists to plan your perfect holiday or request a free quote in just 60 seconds
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Request your free
quote in just 60 seconds